The Ultimate Guide to Managing Difficult Conversations Remotely

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The Ultimate Guide to Managing Difficult Conversations Remotely

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Your direct report Joe has been missing deadlines.

You’ve looked at the situation from all angles. Joe’s missed deadlines are a regular occurrence, not a one-off fluke. You’ve communicated your concerns and detailed your expectations. Still, Joe continues to miss deadlines.

It’s time to talk. But how? When? What if he gets angry? What if I’m missing something?

And the biggest question: How can I go about managing difficult conversations remotely?

As a manager, you’re responsible for coaching your employees to success, which often comes with managing difficult conversations along the way. Even if you or your employee are remote, these difficult conversations must be had. Not only for the success of the business and your team but also for the success of your employee.

Managing difficult conversations, even while remote, can help Joe become better in his job. It also helps your team become more effective and you become a stronger leader.

But, difficult conversations need to be approached gracefully and tactfully to ensure employees don’t become overly defensive and understand what you’re trying to say.

Here are a few best practices to help you connect with your employees in a meaningful way while managing difficult conversations virtually: 

The golden rules of managing difficult conversations remotely

1. Tackle Difficult Conversations Head-On

Difficult conversations are just that…difficult. While our natural insights might encourage us to shy away from confrontation, avoiding these crucial conversations can cause more harm than good.

If employees aren’t aware of issues, they will just continue behaving the same, blissfully unaware that their actions are affecting others. Or, refusing to address small issues when you first notice them can cause them to balloon up and cause even large challenges for your team.

Instead of avoiding difficult conversations, try to take a proactive approach by addressing issues immediately as they arise. What seems like a large issue, might just take 5-minutes of candid conversation to resolve.

2. Don’t Rush It

When it comes to managing difficult conversations, never rush to confront an employee. Take time to process the situation and your emotions, that way you can come prepared with a plan and approach the conversation with a level head.

When you discover there is an issue, step back and take a breath. Then, ask yourself these questions:

  • Is this employee failing to meet the expectations outlined for their role?
  • Is this employee failing to act by our company values?
  • Is this employee making others uncomfortable?
  • Does this employee seem unhappy, unmotivated, or disengaged?

If you answer predominantly yes, it’s time to have a talk. First, spend time identifying and confirming your assumptions with facts – never have a conversation based on rumors or hearsay. Managing difficult conversations requires the same preparation as an interview: draft your talking points and your ideal outcome.

3. Establish Trust

Having mutual trust and respect with your employee is your “emotional bank account.” This process takes time and needs to start long before a candid conversation.

Still, a strong manager-employee relationship makes managing difficult conversations so much easier. Your employees will respect your opinion right off the bat, understand you want to see them succeed, and earnestly want to improve. 

It’s important to note that earning that mutual trust and respect will look different for each employee. Some employees might want you to be a more hands-on manager, others might thrive when given more space.

Figuring out the best ways to support your individual employees as a manager is key to managing difficult conversations. You’ll know the best way to approach each of your employees and the best way to ensure your feedback lands positively. 

A team lead sitting at her desk managing difficult conversations
Photo by Ekaterina Bolovtsova on Pexels

How to have a difficult conversation virtually

1. Have It ‘In-Person’

Don’t have difficult conversations over e-chat or email. Talking on a video call is ideal and can help make the conversation feel as ‘in person’ as possible. A phone call is a solid second option if bandwidth issues are making your video conferencing spotty.

A video call lets you read your employee’s body language and connect with them on a more personal level. It’s harder to deflect the topic at hand over video chat, so it can help you have a more meaningful conversation.

2. Come With a Plan

Never try to just “wing it.” When it comes to managing difficult conversations, you need to come prepared with a list of talking points and specific examples to help guide your conversation and ensure you get your point across.  Here are a few best practices for managing difficult conversations remotely:

  • Give feedback on the behavior, not the person. For example, you’ll tell Joe “I’ve noticed these three projects have all finished after the deadline” instead of saying “You’re disregarding my deadlines.” Sticking with the facts can make it harder for employees to dispute or dismiss your comments. 
  • Reiterate your intentions. Remember the goal of the conversation: you don’t want to reprimand your employees, you want to help them succeed. In our example, the manager would tell Joe that he’s “here to help Joe complete projects and reach deadlines as successfully and efficiently as possible.”
  • Use your conversation as a coaching opportunity. Giving feedback can be a teaching opportunity. Work with Joe to identify what needs to change and how.

3. Let Them Share Their Side

When managing difficult conversations, don’t forget to make time to let your employee speak. Ask broad questions like, “What do you think about all this?” or “Is there anything I should know about that has been impacting your behavior recently?”

Hearing their side of the story might give you additional context that can help you both come to an agreement. For example, when our manager asks Joe if there is anything that might be keeping him from meeting deadlines, he reveals that on top of his day job, he’s been taking care of his ailing mother for the last few weeks.

He often has to step away from his work during the day to help her and hasn’t been sleeping well because he’s been worried about her. All this, he says, has been wearing on him and causing projects to slip through the cracks.

Now that you know Joe’s situation, you can lead with empathy and find a resolution together. You might tell Joe to work flexible hours, so he can help his mother in the middle of the day, or suggest he take paid time off or family leave to care for her in the meantime. Showing him you’re listening to his concerns and trying to accommodate his needs can be just what Joe needs to get back on track.

A manager comes prepared with notes and an agenda for a tough conversation with an employee
Photo by Katerina Holmes on Pexels

4. Be Mindful of Time Zones

Managing difficult conversations isn’t all about what you say – when you say it also matters.

Say Joe works on the West Coast, three hours behind you on the East Coast. Make sure you schedule your call during Joe’s working hours — no one wants to hear difficult feedback at 7 a.m. If someone has to wake up a little early or stay online a little last, it should be you.

5. Over-Communicate

The point of having a difficult conversation is not to chastise your direct report. It’s to show that you care about his success and are here to help. In-person, you can rely on body language, tone, and facial expressions to drive that point home. On a call, you don’t have those luxuries.

Drive your point home by overcommunicating your intentions. Recognize that this conversation is more difficult over video or phone. Reaffirm your intentions in having this conversation a few times and assure them you’re here to help.

When managing a difficult conversation, you want your direct report to understand that you’re on their side. You want to work together with them to come to a resolution that works for everyone. 

6. Follow Up

Once you’ve found a resolution together, close the meeting by recapping both of your commitments, obligations, and agreements.

As a manager, will you remind Joe of deadlines sooner than a day before the project is due? Will Joe take the time off he needs to help his family? Or, raise his hand when he needs help or thinks he will miss an approaching deadline? 

When it comes to managing difficult conversations, don’t just make these commitments, and then wash your hands of the conversation. Schedule a follow-up chat, or address it in your existing 1-on-1 meetings, shortly after your initial conversation to touch base on progress and see if the issues remain unresolved.

You want to keep this conversation active — that’ll show your direct report that you’re invested in helping them address this feedback and have a successful career at your company.

Overseeing a remote team comes with a variety of challenges — managing difficult conversations is one of them. Follow these tips to keep the process smooth and see great results. You’ll find that holding these difficult conversations helps your direct report, team, and yourself grow and improve.

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